CN113563550A - Self-repairing intrinsic stretchable luminescent elastomer and preparation method and application thereof - Google Patents

Self-repairing intrinsic stretchable luminescent elastomer and preparation method and application thereof Download PDF

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CN113563550A
CN113563550A CN202110697696.8A CN202110697696A CN113563550A CN 113563550 A CN113563550 A CN 113563550A CN 202110697696 A CN202110697696 A CN 202110697696A CN 113563550 A CN113563550 A CN 113563550A
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CN113563550B (en
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赖文勇
周婧涵
刘绪
徐世豪
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Nanjing University of Posts and Telecommunications
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Abstract

The invention discloses a self-repairing intrinsic stretchable luminescent elastomer and a preparation method and application thereof. The elastomer is prepared by taking an organic luminescent monomer and bis (amine) terminated poly (dimethylsiloxane) as raw materials and performing cross-linking polymerization through Schiff base reaction. The invention introduces reversible dynamic imine bonds into the intrinsic stretchable luminescent elastomer through Schiff base reaction, realizes the self-repairability of the elastomer through the fracture recombination of the imine bonds, has the self-repairability while the elastomer has the stretchable luminescent property, and solves the problem that the rigid luminescent unit has the stretchability and the self-repairability simultaneously. The preparation method is simple, the monomer source is wide, the cost is low, the product is easy to purify, the yield is high, and the preparation method has important potential application value in the fields of stretchable sensors, stretchable electroluminescent devices, wearable devices, biomedicine and the like.

Description

Self-repairing intrinsic stretchable luminescent elastomer and preparation method and application thereof
Technical Field
The invention belongs to the field of photoelectric information materials and application, and particularly relates to a self-repairing intrinsic stretchable luminescent elastomer, and a preparation method and application thereof.
Background
Self-repairability is an intelligent attribute capable of automatically recovering original appearance and performance after being damaged by the outside. Electronic products are rigid and fragile materials, and the rise of the field of flexible and stretchable electronics enables the electronic products to be light and portable. However, flexible stretchable electronic materials cannot resist device failure due to accidental mechanical damage such as repeated wear and cut scratches, and therefore, there is a need to develop materials having self-repairability and use them in stretchable electronic devices.
Currently, researchers have reported that some hydrogels or elastomers with hydrogen bonds can achieve the self-repairability of elastomers through the bond-breaking recombination of hydrogen bonds, but unfortunately, these hydrogels or elastomers do not possess photophysical properties, which limits their application in the field of stretchable electronic displays. As a core luminescent functional layer material in the field of stretchable photoelectric display, high requirements are required on photophysical properties, stretchability and mechanical toughness, and in order to enable the luminescent functional layer to be repeatedly utilized and prolong the service life, self-repairability is required to be introduced into the luminescent functional layer by a physical or chemical method. In principle, the self-repairability of the material can be realized by embedding the self-repairability into the stretchable luminescent functional layer in a doping mode, however, the introduction of the self-repairability while ensuring the photophysical property and the stretchability of the material has great difficulty in structural design, so that the self-repairability intrinsic stretchable luminescent material is not reported yet. The application discloses an imine bond-based self-repairing intrinsic stretchable luminescent elastomer which is applied to a self-repairing stretchable photoelectric display device as a luminescent functional layer. The intrinsic stretchable luminescent elastomer with self-repairability realizes the self-repairing performance of the stretchable luminescent elastomer in a chemical crosslinking mode without doping. The elastomer is tested and analyzed according to photophysical properties, mechanical properties and self-repairing properties, and the photophysical properties, the mechanical properties and the self-repairing properties of the elastomer are optimally balanced by adjusting the crosslinking ratio and the reaction time of the luminescent monomer and the elastomer.
Disclosure of Invention
The technical problem is as follows:
the invention discloses a self-repairing intrinsic stretchable luminescent elastomer based on an imine structure and a preparation method thereof. The invention introduces self-repairability into the stretchable luminescent elastomer in a chemical crosslinking mode, prepares elastomers with excellent photophysical characteristics, stretchability and self-repairability, and provides a solution for prolonging the service life of a stretchable photoelectric display device, repairing the damage of a photoelectric device and the like.
The technical scheme is as follows:
the invention provides a self-repairing intrinsic stretchable luminescent elastomer based on an imine structure, the structural formula of the elastomer is shown as the following general formula,
Figure BDA0003129179280000021
wherein m is an integer of 3 or more, n is an integer of 20 to 2000, and Ar is a rigid light-emitting unit comprising at least three aldehyde groups.
In one embodiment, the elastomer structure is represented by formula I or formula II:
Figure BDA0003129179280000022
Figure BDA0003129179280000031
wherein n in the structural general formulas I and II is an integer more than 20 and less than 2000, and Ar in the structural general formulas I and II is a rigid luminescent unit at least comprising three or four aldehyde groups.
In one embodiment, Ar in structural formula i and structural formula ii are each independently selected from one of the following structures Ar 1-Ar 48:
Figure BDA0003129179280000032
Figure BDA0003129179280000041
Figure BDA0003129179280000051
Figure BDA0003129179280000061
Figure BDA0003129179280000071
in one embodiment, the elastomer is of the structure:
Figure BDA0003129179280000072
Figure BDA0003129179280000081
Figure BDA0003129179280000091
Figure BDA0003129179280000101
Figure BDA0003129179280000111
Figure BDA0003129179280000121
Figure BDA0003129179280000131
the invention also provides a preparation method of the self-repairing intrinsic stretchable luminescent elastomer, which is characterized by comprising the following steps of using the rigid luminescent unit Ar at least comprising three aldehyde groups and the polymer bis (amine) -terminated poly (dimethylsiloxane) as raw materials, and carrying out chemical crosslinking of the luminescent unit and a polymer long chain through Schiff base reaction to prepare the intrinsic stretchable luminescent elastomer with self-repairing performance, wherein the reaction equation is shown as the following formula III or formula IV:
Figure BDA0003129179280000132
Figure BDA0003129179280000141
in one embodiment, the preparation method of the self-repairing intrinsic stretchable luminescent elastomer is carried out according to the following steps:
(1) dissolving a rigid light-emitting unit Ar and polymer bis (amine) -terminated poly (dimethylsiloxane) in an organic solvent to obtain a reaction solution;
(2) after the reaction is finished, cooling the prepared reaction liquid to room temperature, evaporating the solvent for concentration, dropwise adding the reaction liquid into a large amount of glacial methanol for sedimentation and suction filtration, and drying to obtain the elastomer which is the target product.
The application also provides an application of the self-repairing intrinsic stretchable luminescent elastomer.
In one embodiment, the self-repairing intrinsic stretchable luminescent elastomer is applied to devices such as flexible display devices, biological sensing devices or wearable electronic skins.
In one embodiment, the self-healing intrinsically stretchable luminescent elastomer serves as a luminescent functional layer, an interfacial functional layer, an elastomeric material, or an adjunct ingredient.
Has the advantages that:
the invention provides a self-repairing intrinsic stretchable luminescent elastomer based on an imine structure and a preparation method thereof. The intrinsic stretchable luminescent elastomer prepared by chemically crosslinking the organic luminescent unit and the elastomer has excellent stretching characteristics and good photophysical characteristics, and the introduction of the dynamic imine bond enables the stretchable luminescent elastomer to realize the self-repairability of the elastomer through the broken bond recombination of the imine bond.
The elastomer of the invention simultaneously solves the problems that the rigid luminous unit is not stretchable and has no self-repairing performance. The elastomer has a simple structure, is easy to prepare, has excellent photophysical characteristics, thermal stability and intrinsic stretchability, and has important potential application value in the stretchable photoelectric field.
The intrinsic stretchable luminescent elastomer with self-repairability realizes the self-repairing performance of the stretchable luminescent elastomer in a chemical crosslinking mode without doping. The elastomer is tested and analyzed according to photophysical properties, mechanical properties and self-repairing properties, and the photophysical properties, the mechanical properties and the self-repairing properties of the elastomer are optimally balanced by adjusting the crosslinking ratio and the reaction time of the luminescent monomer and the elastomer.
Drawings
FIG. 1, elastic body PA1 original tensile test and tensile test curve graph after self-repairing
FIG. 2 is a fluorescent emission graph of luminescent monomer Ar1 and elastomer PA1
FIG. 3 self-healing display of elastomer PA1
Detailed Description
The present invention is further illustrated by the following specific examples.
The self-healing intrinsic stretchable luminescent elastomer provided by the embodiment can be in the following structure:
Figure BDA0003129179280000151
Figure BDA0003129179280000161
Figure BDA0003129179280000171
Figure BDA0003129179280000181
Figure BDA0003129179280000191
Figure BDA0003129179280000201
Figure BDA0003129179280000211
examples 1 to 1
Preparation of elastomer PA 1:
Figure BDA0003129179280000212
ar1(13.16mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction was completed, the reaction solution was concentrated by evaporation and dropwise added to a large amount of glacial methanol to be settled, suction-filtered, and dried to obtain elastomer PA1(359mg, yield 35%).
Examples 1 to 2
Preparation of elastomer PA 2:
Figure BDA0003129179280000213
ar2(15.74mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction was completed, the reaction solution was concentrated by evaporation and dropwise added to a large amount of glacial methanol to precipitate, suction-filtered, and dried to obtain elastomer PA2(350mg, yield 34%).
Examples 1 to 3
Preparation of elastomer PA 3:
Figure BDA0003129179280000221
ar3(22.28mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction, the reaction solution was concentrated by evaporation and added dropwise to a large amount of glacial methanol to precipitate, suction-filtered, and dried to obtain elastomer PA3(589mg, yield 57%).
Examples 1 to 4
Preparation of elastomer PA 8:
Figure BDA0003129179280000222
ar8(57.08mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction was completed, the reaction solution was concentrated by evaporation and dropwise added to a large amount of glacial methanol to precipitate, suction-filtered, and dried to obtain elastomer PA8(451mg, yield 42%).
Examples 1 to 5
Preparation of elastomer PA 11:
Figure BDA0003129179280000231
ar11(63.88mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction was completed, the reaction solution was evaporated and concentrated and dropwise added to a large amount of glacial methanol to precipitate, suction-filtered, and dried to obtain elastomer PA11(689mg, yield 64%).
Examples 1 to 6
Preparation of elastomer PA 12:
Figure BDA0003129179280000232
ar12(22.8mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction was completed, the reaction solution was concentrated by evaporation and dropwise added to a large amount of glacial methanol to be settled, suction-filtered, and dried to obtain elastomer PA12(725mg, yield 70%).
Examples 1 to 7
Preparation of elastomer PA 18:
Figure BDA0003129179280000241
ar18(28.7mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction, the reaction mixture was concentrated by evaporation and added dropwise to a large amount of glacial methanol to precipitate, suction-filtered and dried to give elastomer PA18(737mg, 71% yield).
Examples 1 to 8
Preparation of elastomer PA 20:
Figure BDA0003129179280000242
ar20(22.8mg,0.04mmol) and a (1000mg,0.04mmol) were placed in a 50mL two-necked flask, which was sealed with a rubber stopper. After 10mL of a methylene chloride solvent was injected into the flask, the apparatus was stirred at room temperature for 48 hours. After the reaction, the reaction solution was concentrated by evaporation and added dropwise to a large amount of glacial methanol to precipitate, suction-filtered, and dried to obtain elastomer PA20(569mg, yield 55%).
Example 2-1
Preparation of organic light-emitting diode device:
preparation of organic light-emitting diode device: ITO (indium tin oxide) glass is subjected to ultrasonic cleaning and then is treated by oxygen plasma, a hole injection layer is PEDOT: PSS (poly 3, 4-ethylenedioxythiophene-polystyrene sulfonic acid), and a light-emitting layer is made of a self-repairing intrinsic stretchable light-emitting elastomer PA 1. The hole injection layer and the luminescent layer are both prepared in a mode of spin coating by solution. The cathode electrode is made of LiF/Al. The maximum luminous brightness of the OLED device prepared based on PA1 is 8763cd/m2The lighting voltage was 3.9V.
Examples 2.2 to 2.8
Preparation of organic light-emitting diode device:
an organic light-emitting diode device was produced in the same manner as in example 2-1, except that each elastomer described in table 1 was used as the light-emitting layer instead of elastomer PA 1. For the obtained organic light emitting diode device, the device turn-on voltage, the fluorescent luminance and the elastomer self-repair efficiency were measured in the same manner as in example 2-1, and the results are shown in table 1.
TABLE 1
Examples Luminous elastic body Efficiency of elastomer self-repair Lighting voltage (V) Fluorescence luminance (cd/m)2)
2-1 PA1 62％ 3.9 8763
2-2 PA2 67％ 5.68 5645
2-3 PA3 55％ 9.3 4568
2-4 PA8 45％ 8.5 4876
2-5 PA11 57％ 4.1 7658
2-6 PA12 58％ 9.2 5879
2-7 PA18 69％ 7.6 3754
2-8 PA20 48％ 5.8 8190
The tensile test curve and the tensile test curve after self-repairing of the elastomer PA1 are shown in figure 1, the original tensile multiple of the elastomer PA1 is 40 times, the elastomer can be stretched by 25 times after fracture self-repairing, and the self-repairing rate is about 62%, which shows that the elastomer has excellent self-repairing performance; FIG. 2 shows fluorescence emission spectra of the elastomer PA1 and the rigid luminescent unit Ar, wherein the fluorescence spectrum of the elastomer PA1 is obviously blue-shifted relative to the fluorescence spectrum of the rigid luminescent unit Ar1, because the energy of photons in the elastomer is increased and the wavelength is shortened after the rigid luminescent unit is polymerized, so that the emission spectrum of the elastomer is blue-shifted; fig. 3 shows a self-repairing process of the elastomer PA1, and it can be seen from fig. 3 that the elastomer still has mechanical properties to a certain extent after being self-repaired.
The above are embodiments of the present invention, it should be noted that the present invention is not limited to these examples, and these examples are only for better understanding of the present invention, and any equivalent changes made according to the technical scheme of the present invention are within the protection scope of the present invention.

Claims (8)

1. A self-repairing intrinsic stretchable luminescent elastomer is characterized in that the structural formula of the elastomer is shown as the following general formula,
Figure FDA0003129179270000011
，
wherein m is an integer of 3 or more, n is an integer of 20 to 2000, and Ar is a rigid light-emitting unit comprising at least three aldehyde groups.
2. The self-healing intrinsic stretchable luminescent elastomer according to claim 1, characterized in that the structural formula of the elastomer is represented by general formula i or general formula ii:
Figure FDA0003129179270000012
Figure FDA0003129179270000021
wherein n in the general formula I and the general formula II is an integer of 20-2000, and Ar is a rigid luminescent unit containing three or four aldehyde groups.
3. The self-repairing intrinsically stretchable luminescent elastomer of claim 1, wherein the rigid luminescent units Ar in the general structural formulas I and II are each independently selected from one of the following structures Ar 1-Ar 48:
Figure FDA0003129179270000022
Figure FDA0003129179270000031
Figure FDA0003129179270000041
Figure FDA0003129179270000051
Figure FDA0003129179270000061
4. the self-healing intrinsically stretchable luminescent elastomer of claim 1, characterized in that the elastomer has the structure:
Figure FDA0003129179270000062
Figure FDA0003129179270000071
Figure FDA0003129179270000081
Figure FDA0003129179270000091
Figure FDA0003129179270000101
Figure FDA0003129179270000111
Figure FDA0003129179270000121
5. a method of making the self-healing intrinsically stretchable luminescent elastomer of claim 1,
the preparation method is characterized by comprising the following steps:
the elastomer takes rigid luminescent unit Ar at least comprising three aldehyde groups and bis (amine) -terminated poly (dimethylsiloxane) as construction units, and the rigid luminescent unit and the polymer bis (amine) -terminated poly (dimethylsiloxane) are chemically crosslinked through Schiff base reaction under the condition of stirring at room temperature to prepare the self-repairable intrinsic stretchable luminescent elastomer, wherein the reaction equation is shown as the following formula III or formula IV:
Figure FDA0003129179270000122
Figure FDA0003129179270000131
6. the method of claim 5, comprising the steps of:
(1) dissolving a rigid light-emitting unit Ar and polymer bis (amine) -terminated poly (dimethylsiloxane) in an organic solvent, and stirring at room temperature to obtain a reaction solution;
(2) after the reaction is finished, concentrating the prepared reaction solution, dropwise adding the reaction solution into a methanol solvent for settling, and performing suction filtration and drying to obtain the target product elastomer.
7. The method for preparing the self-repairing intrinsic stretchable luminescent elastomer as claimed in claim 6, wherein the organic solvent is dichloromethane, tetrahydrofuran, toluene, chloroform or acetone.
8. The use of the self-healing intrinsically stretchable luminescent elastomer of claim 1, wherein the elastomer is used as a luminescent functional layer, an interfacial functional layer, an elastomeric material or an auxiliary component in a flexible display device, a biosensing device or a wearable electronic skin device.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108504021A (en) * 2017-02-28 2018-09-07 中国科学院化学研究所 A kind of dimethyl silicone polymer selfreparing elastomer and preparation method thereof based on acylhydrazone key
CN108546337A (en) * 2018-05-16 2018-09-18 中国船舶重工集团公司第七二五研究所 A kind of organosilicon selfreparing anti-fouling material preparation method
CN110358032A (en) * 2019-07-15 2019-10-22 青岛科技大学 It is a kind of based on imine linkage can selfreparing, recyclable elastomer silicone and preparation method thereof
US20200002501A1 (en) * 2018-06-29 2020-01-02 Samsung Electronics Co., Ltd. Self-healing composite and device including self-healing film
CN113004477A (en) * 2021-02-25 2021-06-22 中国林业科学研究院林产化学工业研究所 Schiff base-based plant oil-based self-repairing polymer and preparation method and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108504021A (en) * 2017-02-28 2018-09-07 中国科学院化学研究所 A kind of dimethyl silicone polymer selfreparing elastomer and preparation method thereof based on acylhydrazone key
CN108546337A (en) * 2018-05-16 2018-09-18 中国船舶重工集团公司第七二五研究所 A kind of organosilicon selfreparing anti-fouling material preparation method
US20200002501A1 (en) * 2018-06-29 2020-01-02 Samsung Electronics Co., Ltd. Self-healing composite and device including self-healing film
CN110358032A (en) * 2019-07-15 2019-10-22 青岛科技大学 It is a kind of based on imine linkage can selfreparing, recyclable elastomer silicone and preparation method thereof
CN113004477A (en) * 2021-02-25 2021-06-22 中国林业科学研究院林产化学工业研究所 Schiff base-based plant oil-based self-repairing polymer and preparation method and application thereof

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